Concept explainers
(a)
Interpretation:
Resonance contributor for the enolate ion formed from the given compounds has to be identified.
Concept Introduction:
Tautomerism is the ability of a molecule to exist in more than one chemical form. Tautomers are formed by the migration of a hydrogen atom, accompanied by the switching of a single and neighboring double bond.
The only difference in keto-enol tautomers is the location of hydrogen and double bond.
Enol tautomer is much less stable than the keto tautomer.
Enol tautomer is more stable when enol tautomer is
Resonance: The delocalization of electrons which is characterized as several structural changes.
(b)
Interpretation:
Resonance contributor for the enolate ion formed from the given compounds has to be identified.
Concept Introduction:
Tautomerism is the ability of a molecule to exist in more than one chemical form. Tautomers are formed by the migration of a hydrogen atom, accompanied by the switching of a single and neighboring double bond.
The only difference in keto-enol tautomers is the location of hydrogen and double bond.
Enol tautomer is much less stable than the keto tautomer.
Enol tautomer is more stable when enol tautomer is aromatic or when the double bonds are conjugated.
Resonance: The delocalization of electrons which is characterized as several structural changes.
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Chapter 13 Solutions
EP ESSENTIAL ORG.CHEM.-MOD.MASTERING
- Draw the keto form of the following enol.arrow_forwardWhat aldehyde or ketone would be obtained when the following compound is heated in a basic aqueous solution? 2,4-dicyclohexyl-3-hydroxybutanalarrow_forwardWhat is the role of triethylamine in this reaction? Draw the curly arrow reaction mechanism to show bonds being broken/formed.arrow_forward
- Draw the structure of the aromatic product from the following reaction. но H2N° 1 equivalentarrow_forwardConsider the following reaction: Br ELOH i) How would the rate of reaction be affected if the concentration of the tert-butyl bromide is doubled? ii) How would the rate of reaction be affected if the concentration of the EtOH is doubled?arrow_forwardThe following molecule undergoes an intramolecular reaction in the presence of pyrro- lidinium acetate, the protonated form of pyrrolidine. Draw the product of this reaction, assuming that a dehydration reaction takes place. Me Me Но N: 'N' AcO Ме pyrrolidinium acetate Me Me Mearrow_forward
- Rank the following compounds in order of increasing basicity and explain the order you chose.arrow_forwardWhich one of the following carboxylic acid derivatives can undergo nucleophilic acyl substitution without the need of an acid to catalyze the reaction? O CH3C=N ОН `NH2arrow_forwardIdentify the acetal in oleandrin, the chapter-opening molecule, and draw the products formed by acid-catalyzed hydrolysis of the acetal.arrow_forward
- Name the carbonyl compound that would be formed by the complete acidic hydrolysis of the following hemiacetal/hemiketal or acetal/ketal: OH OCH₂CH₂CH₂CH₂CH3arrow_forwardRank the reactivity of the compounds below toward nucleophilic acyl substitution by writing the compounds' letters in the proper blanks in the box below. `NH CI Br CH3 CH3 A В C E rank compounds for acyl substitution reactivity most least reactive reactivearrow_forwardRank the following esters in order of decreasing reactivity in the first slow step of a nucleophilic acyl substitution reaction (formation of the tetrahedral intermediate):Rank the same esters in order of decreasing reactivity in the second slow step of a nucleophilic acyl substitution reaction (collapse of the tetrahedral intermediate).arrow_forward
Organic ChemistryChemistryISBN:9781305580350Author:William H. Brown, Brent L. Iverson, Eric Anslyn, Christopher S. FootePublisher:Cengage Learning